Cheap Flights to Chester from $57

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How Much Does it Cost To Fly To Chester?

The cheapest prices found with in the last 7 days for return flights were $122 and $57 for one-way flights to Chester for the period specified. Prices and availability are subject to change. Additional terms apply

Fri, Dec 5 - Mon, Dec 8
CHS
Charleston Intl.
SWF
Stewart Intl.
$122 Roundtrip, found 9 hours ago
$122
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Fri, Dec 5 from Charleston Intl. to Stewart Intl., returning Mon, Dec 8, priced at $122 found 9 hours ago
OriginDestinationTravel DatesFlights From*
MCONewburghSeptember 11 to September 18$122
SFONewburghSeptember 14 to September 19$657
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCONewburghAugust 24 to September 4$264
LAXNewburghAugust 24 to September 1$765
*Prices include taxes and fees

Chester Flight Information

Traveling to
Chester
Lowest Price
$122
Number of Airlines Serving
Airlines Serving
Breeze Airways
Number of Daily Flights
Airlines with Direct Flights

Flight Review

Dec 14, 2018

Main cabin & “comfort” seats painfully cramped. Had to upgrade (and pay) so I could cross my legs

A verified traveler
Raleigh to New York · Delta
Mar 25, 2018

Great flight attendants on both flights.

A verified traveler
Raleigh to Newark · United

Find The Perfect Hotel For After Your Flight

Family Friendly Hotels in Chester

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
2 Bryle Place, Chester, NY
$139 nightly
The price is $164 total per night from Sep 14 to Sep 15
$164 total
Sep 14 - Sep 15
Total includes taxes and fees
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,003 reviews)
"The hotel was great, but I specifically booked it for the pool for my children, and for two days of our 4-day trip it was closed. Other wise a nice location and I would return again."

Reviewed on Aug 16, 2025

Holiday Inn Express Hotel & Suites Chester by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Best Chester Flight and Hotel Packages

Chester flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
The Lagrange Inn & Extended Stay

The Lagrange Inn & Extended Stay

2 out of 5
Save 100% on your flight
Price was $443, price is now $349 per person
$349
per person
Oct 11 - Oct 15
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Newburgh (SWF)
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
Price was $415, price is now $373 per person
$373
per person
Sep 25 - Sep 28
found 17 hours ago
Roundtrip flight included
Chicago (ORD) to Newburgh (SWF)
Don't see what you're looking for?
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Need a Car For After Your Flight?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Chester?
20 airlines offer flights to the city of Chester, making it one of the world's most frequented airline hubs. Most savvy travelers choose to fly with these carriers:

  • Delta Air Lines
  • United Airlines
  • American Airlines

What airport is best to fly into Chester?
Who looks forward to getting stuck in bumper-to-bumper traffic while on their way to a flight on the opposite end of the city? Wander wisely. Chester is serviced by a few airports, so consider which one is closest to where you'll be spending most of your time. Here are the city's key airports:

  • John F. Kennedy Intl. Airport (JFK) – 55 mi from downtown
  • EWR – 45 mi from downtown
  • LaGuardia Airport – 45 mi from downtown

Where to stay in Chester
Whether you're visiting Chester on a family vacation, for work or something else, we're confident you'll find the perfect place to crash. Travelocity offers at least 66 accommodations within easy reach of the heart of town.The Holiday Inn Express Hotel & Suites Chester, an IHG Hotel and the Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries are our top accommodations in Chester. Make a reservation and then get down to the fun stuff — booking your amazing getaway experiences.
Places to visit in Chester
Take a look at the schedule for The Rock Sports Complex, where you can enjoy an exciting sports match. Need some more ideas? Free up an afternoon and get your game on at Castle Fun Center. And that's not all there is. Keep an eye out for wildlife, sharpen your photography skills and stroll through nature at Goosepond Mountain State Park.
How to get through airport security fast when traveling to Chester
Make your flight to Chester a little bit easier by following these useful security tips:

  • Keep your travel ID and boarding pass in an easily accessible place. They'll be the first things you'll be asked for by airport security staff.
  • USB sticks, wallets and power banks must be put in a bin for X-raying. If you pass through the body scanner with any of these items, you'll be asked to turn back and remove them.
  • Digital cameras, laptops and other electronic devices must be placed in separate bins to be X-rayed.
  • When you approach the security checkpoint, you'll be asked to place all creams, gels and liquids in a separate tub for inspection. Make sure they're all in containers no larger than 3.4 ounces (100 milliliters) and sealed in a clear zip-lock bag.
  • Construction boots and other cumbersome shoes are usually X-rayed at the security checkpoint. It might be wise to wear simple sneakers instead.
  • Pack any pocketknives or other pointy metal items inside your checked luggage. Security personnel don't allow these on the aircraft.

Plane Tickets To Chester

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Chester. Browse through our inventory to explore a wide range of cheap flights to Chester to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Chester as you anxiously await to exit the plane and explore what Chester has to offer. Considering all the amazing local food and culture in Chester, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Chester to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Chester without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Chester with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Chester today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.